We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Guanidiniocarbonyl Pyrrole Cation (GCP) – A New Guest for Cucurbit[8]uril: Application to the Synthesis of Supramolecular Polymers Based on CB[8]@2GCP Complex Formation.
- Authors
Samanta, Krishnananda; Sicking, Wilhelm; Schmuck, Carsten
- Abstract
Herein we introduce a new guest, the guanidiniocarbonyl pyrrole cation (GCP), for host–guest chemistry with cucurbit[8]uril. Macromodel calculations as well as isothermal titration calorimetry (ITC), showed that CB[8] can entrap two GCP molecules inside its hydrophobic cavity. Using this 1:2‐complex formation, we further show that CB[8] can induce crosslinking of a flexibletetracationic guanidiniocarbonyl pyrrole. An extended supramolecular cross‐linked 3D network was observed at pH 4.1 where all GCP groups in guanidiniocarbonyl pyrrole are protonated. At pH 6.5, the GCP groups are only partially protonated nanostructures with a more globular vesicle‐like shape. Cucurbituril[8] is an efficient host for two GCP cations. Addition of CB[8] to a tetra‐GCP compound 1 thus induces supramolecular polymerization. Depending on the pH and the protonation state of the GCP cation different types of aggregates are formed.
- Subjects
PYRROLES; CUCURBITURIL; SUPRAMOLECULAR polymers synthesis; HOST-guest chemistry; ISOTHERMAL titration calorimetry
- Publication
European Journal of Organic Chemistry, 2018, Vol 2018, Issue 46, p6515
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201801210